#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009045.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009045
loop_
_publ_author_name
'Ishida, H.'
'Kashino, S.'
_publ_section_title
;
 1:2 Complexes of chloranilic acid with pyrimidine and pyrazine
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1714
_journal_page_last               1717
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         '2C4 H4 N2, C6 H2 Cl2 O4'
_chemical_formula_sum            'C14 H10 Cl2 N4 O4'
_chemical_formula_weight         369.16
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 94.48(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.8283(7)
_cell_length_b                   18.514(5)
_cell_length_c                   10.795(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      10.9
_cell_volume                     762.8(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection
'MSC/AFC Diffractometer Control (Molecular Structure Corporation, 1990)'
_computing_data_reduction
'TEXSAN for Windows (Molecular Structure Corporation, 1997)'
_computing_publication_material  'TEXSAN for Windows'
_computing_structure_refinement  'TEXSAN for Windows'
_computing_structure_solution
;
SIR92 (Altomare et al., 1993)
;
_diffrn_ambient_temperature      296
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_av_sigmaI/netI    0.114
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2054
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.9
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type
;
\y scans (North et al., 1968)
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.00
_refine_diff_density_min         -0.90
_refine_ls_extinction_coef       0.0000028(3)
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   1.37
_refine_ls_goodness_of_fit_ref   1.37
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1731
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.117
_refine_ls_R_factor_gt           0.065
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00004|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.092
_refine_ls_wR_factor_ref         0.061
_reflns_number_gt                877
_reflns_number_total             1799
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ob1011.cif
_[local]_cod_data_source_block   2
_[local]_cod_cif_authors_sg_H-M  'P 21/n     '
_cod_database_code               2009045
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
1/2-x,1/2+y,1/2-z
'   -x,   -y,   -z'
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Cl 0.7279(3) 0.12075(6) 0.67562(8) 0.0356(3) Uani d 1.000
O1 1.1169(7) -0.01280(10) 0.7450(2) 0.0404(9) Uani d 1.000
O2 0.6310(7) 0.1159(2) 0.3998(2) 0.0375(9) Uani d 1.000
N1 0.5514(8) 0.1481(2) 0.1658(3) 0.0350(10) Uani d 1.000
N2 0.4787(9) 0.1957(2) -0.0789(3) 0.0420(10) Uani d 1.000
C1 1.0580(10) -0.0050(2) 0.6331(3) 0.0270(10) Uani d 1.000
C2 0.8720(10) 0.0557(2) 0.5760(3) 0.0260(10) Uani d 1.000
C3 0.8080(10) 0.0625(2) 0.4512(3) 0.0260(10) Uani d 1.000
C4 0.6610(10) 0.2131(3) 0.1347(4) 0.042(2) Uani d 1.000
C5 0.6240(10) 0.2360(2) 0.0120(4) 0.042(2) Uani d 1.000
C6 0.3680(10) 0.1304(3) -0.0452(4) 0.0400(10) Uani d 1.000
C7 0.4070(10) 0.1063(3) 0.0758(4) 0.0400(10) Uani d 1.000
H1 0.610(10) 0.121(3) 0.302(4) 0.120(10) Uiso d 1.000
H2 0.774(8) 0.243(2) 0.197(3) 0.030(10) Uiso d 1.000
H3 0.710(10) 0.282(2) -0.010(3) 0.050(10) Uiso d 1.000
H4 0.257(9) 0.105(2) -0.113(3) 0.050(10) Uiso d 1.000
H5 0.307(9) 0.064(2) 0.103(3) 0.030(10) Uiso d 1.000
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl 0.0469(7) 0.0345(6) 0.0256(5) 0.0036(7) 0.0034(4) -0.0046(6)
O1 0.066(2) 0.036(2) 0.0190(10) 0.004(2) 0.0000(10) 0.0020(10)
O2 0.057(2) 0.029(2) 0.0250(10) 0.014(2) -0.0030(10) -0.0010(10)
N1 0.044(2) 0.038(2) 0.022(2) 0.006(2) -0.003(2) 0.002(2)
N2 0.058(3) 0.042(2) 0.027(2) 0.003(2) 0.001(2) 0.003(2)
C1 0.030(2) 0.029(2) 0.021(2) -0.006(2) 0.003(2) -0.001(2)
C2 0.030(2) 0.026(2) 0.021(2) -0.002(2) 0.003(2) -0.003(2)
C3 0.029(2) 0.028(2) 0.022(2) -0.004(2) 0.001(2) -0.002(2)
C4 0.046(3) 0.041(3) 0.037(3) 0.006(2) -0.003(2) -0.008(2)
C5 0.054(3) 0.034(3) 0.039(3) 0.010(3) 0.008(2) 0.007(2)
C6 0.044(3) 0.047(3) 0.027(2) 0.003(3) -0.002(2) -0.008(3)
C7 0.044(3) 0.040(3) 0.036(3) -0.005(2) 0.004(2) 0.007(2)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O 0.008 0.006
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
Cl 0.132 0.159
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N 0.004 0.003
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 -3 0
1 3 -1
1 -2 0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O2 H1 . . 119(3) no
O1 C1 C2 . . 124.3(4) yes
O1 C1 C3 . 3_756 117.7(4) yes
C2 C1 C3 . 3_756 118.0(4) yes
Cl C2 C1 . . 116.5(3) yes
Cl C2 C3 . . 120.8(4) yes
C1 C2 C3 . . 122.8(4) yes
O2 C3 C1 . 3_756 117.9(4) yes
O2 C3 C2 . . 122.8(4) yes
C1 C3 C2 3_756 . 119.2(4) yes
N1 C4 C5 . . 120.6(5) yes
N1 C4 H2 . . 119(2) no
C5 C4 H2 . . 120(2) no
N2 C5 C4 . . 122.8(5) yes
C4 N1 C7 . . 117.7(4) yes
C5 N2 C6 . . 115.6(4) yes
N2 C5 H3 . . 117(3) no
C4 C5 H3 . . 120(3) no
N2 C6 C7 . . 122.4(5) yes
N2 C6 H4 . . 112(3) no
C7 C6 H4 . . 126(3) no
N1 C7 C6 . . 120.8(5) yes
N1 C7 H5 . . 115(2) no
C6 C7 H5 . . 124(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C2 . 1.733(4) yes
O1 C1 . 1.219(4) yes
O2 C3 . 1.298(5) yes
O2 H1 . 1.06(5) no
C1 C2 . 1.443(6) yes
C1 C3 3_756 1.517(5) yes
C2 C3 . 1.356(5) yes
N1 C4 . 1.326(6) yes
N1 C7 . 1.329(5) yes
N2 C5 . 1.320(6) yes
N2 C6 . 1.340(6) yes
C4 C5 . 1.387(6) yes
C4 H2 . 0.95(4) no
C5 H3 . 0.96(4) no
C6 C7 . 1.378(6) yes
C6 H4 . 0.94(4) no
C7 H5 . 0.93(4) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_publ_flag
O1 N1 2.938(5) 3_756 no
O2 N1 2.590(4) . no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cl C2 C1 O1 . . 0.2(6) no
Cl C2 C1 C3 . 3_756 -179.2(3) no
Cl C2 C3 O2 . . -2.1(6) no
Cl C2 C3 C1 . 3_756 179.2(3) no
O1 C1 C2 C3 . . -179.6(4) no
O1 C1 C3 O2 3_756 3_756 -1.7(6) no
O1 C1 C3 C2 3_756 3_756 179.6(4) no
O2 C3 C1 C2 3_756 3_756 -177.8(4) no
O2 C3 C2 C1 . . 177.7(4) no
N1 C4 C5 N2 . . 0.6(8) no
N1 C7 C6 N2 . . 1.5(8) no
C4 N1 C7 C6 . . -1.1(7) no
C4 C5 N2 C6 . . -0.3(8) no
C5 N2 C6 C7 . . -0.8(7) no
C5 C4 N1 C7 . . 0.1(7) no